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. Author manuscript; available in PMC: 2016 Sep 21.
Published in final edited form as: Angew Chem Int Ed Engl. 2015 Jul 24;54(39):11424–11427. doi: 10.1002/anie.201504076

Table 2.

[4+2] Annulation of phenylacetylene (2a) with monocyclic cyclobutylanilines.

graphic file with name nihms732628u3.jpg
Entry[a] Substrate Product t [h] Yield[%][b]
1 1b, R = H graphic file with name nihms732628t1.jpg
3b
12 76
2 1c, R = 4-CF3 graphic file with name nihms732628t2.jpg
3c
24 79
3 1d, R = 4-OMe graphic file with name nihms732628t3.jpg
3d
18 27
4 1e, R = 2-CN graphic file with name nihms732628t4.jpg
3e
20 84
5 1f, R = 2-phenyl graphic file with name nihms732628t5.jpg
3f
20 78
6 1g, R = 2-iPr graphic file with name nihms732628t6.jpg
3g
24 73
7 1h graphic file with name nihms732628t7.jpg graphic file with name nihms732628t8.jpg
3h
12 87
8 1i graphic file with name nihms732628t9.jpg graphic file with name nihms732628t10.jpg
3i
14 76
9 1j graphic file with name nihms732628t11.jpg graphic file with name nihms732628t12.jpg
3j
18 83
[a]

Reaction condition: substrate (0.2 mmol, 0.1 M in degassed MeOH), 2a (1 mmol), 4a (2 mol%), irradiation with two 18 W LED light bulbs.

[b]

Yield of the isolated product.